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UC213

Sigma-Aldrich

(R)-(+)-Warfarin

≥97% (HPLC)

Synonyme(s) :

R-(+)-3-Acetonybenzyl)-4-hydroxycoumarin, R-(+)-4-Hydroxy-3-(3-oxo-1-phenybutyl)-2H-1-benzopyran-2-one

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About This Item

Formule empirique (notation de Hill):
C19H16O4
Numéro CAS:
5543-58-8
Poids moléculaire :
308.33
Numéro CE :
226-908-9
Numéro MDL:
MFCD00272376
Code UNSPSC :
12161501
ID de substance PubChem :
24724649

Essai

≥97% (HPLC)

Forme

solid

Couleur

white to pale yellow

Pf

≥170 °C

Solubilité

DMF: soluble
DMSO: soluble
ethanol: soluble

Température de stockage

2-8°C

Chaîne SMILES 

[H][C@@](CC(C)=O)(c1ccccc1)C2=C(O)c3ccccc3OC2=O

InChI

1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3/t15-/m1/s1

Clé InChI

PJVWKTKQMONHTI-OAHLLOKOSA-N

Informations sur le gène

human ... CYP2C9(1559)

Description générale

The chiral carbon at position 9 produces two enantiomers, R- and S-warfarin. Commercially available warfarin (Coumadin or Jantoven) is a racemic mixture of S- and R-enantiomers.

Application

(R)-(+)-warfarin has been used to investigate whether enantiomers of warfarin stereoselectively interact with pregnane X nuclear receptor (PXR) to upregulate main drug/xenobiotic-metabolizing enzymes cytochrome P450 3A4 (CYP3A4) and cytochrome P450 2C9 (CYP2C9). It has also been used in HepG2 cells to study protein profiles

Actions biochimiques/physiologiques

Warfarin acts as a vitamin K antagonist. It is widely used to treat thromboembolic disorders. (R)-warfarin interacts with pregnane X receptor (PXR) and induces cytochrome P450 3A4 (CYP3A4) and CYP2C9 mRNAs expression in primary human hepatocyte cultures.
CYP1A2/3A4 substrate; anticoagulant.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Notes préparatoires

(+)-Warfarin is soluble in DMF, DMSO and ethanol.

Pictogrammes

Skull and crossbonesHealth hazardEnvironment
GHS06,GHS08,GHS09

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Aquatic Chronic 2 - Repr. 1A - STOT RE 1

Organes cibles

Blood

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
483-136-2V
483-136-2
053M3903V
053M3903
1385524

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Consulter la Bibliothèque de documents

Metabolic profiling of HepG2 cells incubated with S(-) and R(+) enantiomers of anti-coagulating drug warfarin
Bai, J, et al.
Metabolomics, 7(3), 353-362 (2011)
A Rulcova et al.
Journal of thrombosis and haemostasis : JTH, 8(12), 2708-2717 (2010-08-26)
Warfarin, an antagonist of vitamin K, is an oral coumarin anticoagulant widely used to control and prevent thromboembolic disorders. Warfarin is clinically available as a racemic mixture of R- and S-warfarin. The S-enantiomer has three to five times greater anticoagulation
Michelle J Yoo et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(11-12), 1149-1154 (2009-03-31)
Binding by the drug imipramine to the protein human serum albumin (HSA) was studied by using high-performance affinity chromatography. The association equilibrium constants and number of binding sites for imipramine with HSA were first estimated by utilizing frontal analysis. Imipramine
Jing Bai et al.
Proteomics. Clinical applications, 4(10-11), 808-815 (2010-12-08)
warfarin is a commonly prescribed oral anticoagulant with narrow therapeutic index. It interferes with the vitamin K cycle to achieve anti-coagulating effects. Warfarin has two enantiomers, S(-) and R(+) and undergoes stereoselective metabolism, with the S(-) enantiomer being more effective.
Konstantin Doronin et al.
Human gene therapy, 20(9), 975-988 (2009-05-28)
Oncolytic adenoviruses are anticancer agents that replicate within tumors and spread to uninfected tumor cells, amplifying the anticancer effect of initial transduction. We tested whether coating the viral particle with polyethylene glycol (PEG) could reduce transduction of hepatocytes and hepatotoxicity
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Protocoles

Chiral and Achiral LC-MS Analysis of Warfarin™ in Plasma Samples

his study demonstrates the analysis of Warfarin in plasma samples utilizing chiral and achiral (reversed-phase) LC-MS and effective sample prep to remove endogenous phospholipids

Chromatograms

application for HPLCapplication for HPLCapplication for HPLCapplication for HPLCAfficher plus

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